Bisucaberin
(Synonyms: NSC 619796) 目录号 : GC49041
A siderophore with anticancer activity
Cas No.:112972-60-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bisucaberin is a siderophore and bacterial metabolite that has been found in A. haloplanktis and has anticancer activity.1,2 It inhibits the growth of L1210 and 1MC carcinoma cells (IC50s = 9.7 and 12.7 µM, respectively) and sensitizes fibrosarcoma 1023 cells to macrophage-mediated cytolysis.
1.Hou, Z., Raymond, K.N., O’Sullivan, B., et al.A preorganized siderophore: Thermodynamic and structural characterization of alcaligin and bisucaberin, microbial macrocyclic dihydroxamate chelating agentsInorg. Chem.37(26)6630-6637(1998) 2.Kameyama, T., Takahashi, A., Kurasawa, S., et al.Bisucaberin, a new siderophore, sensitizing tumor cells to macrophage-mediated cytolysis. I. Taxonomy of the producing organism, isolation and biological propertiesJ. Antibiot. (Tokyo)40(12)1664-1670(1987)
| Cas No. | 112972-60-8 | SDF | |
| 别名 | NSC 619796 | ||
| Canonical SMILES | O=C1N(O)CCCCCNC(CCC(N(O)CCCCCNC(CC1)=O)=O)=O | ||
| 分子式 | C18H32N4O6 | 分子量 | 400.5 |
| 溶解度 | N/A | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4969 mL | 12.4844 mL | 24.9688 mL |
| 5 mM | 0.4994 mL | 2.4969 mL | 4.9938 mL |
| 10 mM | 0.2497 mL | 1.2484 mL | 2.4969 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The chemical biology and coordination chemistry of putrebactin, avaroferrin, Bisucaberin, and alcaligin
J Biol Inorg Chem 2018 Oct;23(7):969-982.PMID:29946977DOI:10.1007/s00775-018-1585-1.
Dihydroxamic acid macrocyclic siderophores comprise four members: putrebactin (putH2), avaroferrin (avaH2), Bisucaberin (bisH2), and alcaligin (alcH2). This mini-review collates studies of the chemical biology and coordination chemistry of these macrocycles, with an emphasis on putH2. These Fe(III)-binding macrocycles are produced by selected bacteria to acquire insoluble Fe(III) from the local environment. The macrocycles are optimally pre-configured for Fe(III) binding, as established from the X-ray crystal structure of dinuclear [Fe2(alc)3] at neutral pH. The dimeric macrocycles are biosynthetic products of two endo-hydroxamic acid ligands flanked by one amine group and one carboxylic acid group, which are assembled from 1,4-diaminobutane and/or 1,5-diaminopentane as initial substrates. The biosynthesis of alcH2 includes an additional diamine C-hydroxylation step. Knowledge of putH2 biosynthesis supported the use of precursor-directed biosynthesis to generate unsaturated putH2 analogues by culturing Shewanella putrefaciens in medium supplemented with unsaturated diamine substrates. The X-ray crystal structures of putH2, avaH2 and alcH2 show differences in the relative orientations of the amide and hydroxamic acid functional groups that could prescribe differences in solvation and other biological properties. Functional differences have been borne out in biological studies. Although evolved for Fe(III) acquisition, solution coordination complexes have been characterised between putH2 and oxido-V(IV/V), Mo(VI), or Cr(V). Retrosynthetic analysis of 1:1 complexes of [Fe(put)]+, [Fe(ava)]+, and [Fe(bis)]+ that dominate at pH < 5 led to a forward metal-templated synthesis approach to generate the Fe(III)-loaded macrocycles, with apo-macrocycles furnished upon incubation with EDTA. This mini-review aims to capture the rich chemistry and chemical biology of these seemingly simple compounds.
Bisucaberin B, a linear hydroxamate class siderophore from the marine bacterium Tenacibaculum mesophilum
Molecules 2013 Apr 2;18(4):3917-26.PMID:23549298DOI:10.3390/molecules18043917.
A siderophore, named Bisucaberin B, was isolated from Tenacibaculum mesophilum bacteria separated from a marine sponge collected in the Republic of Palau. Using spectroscopic and chemical methods, the structure of Bisucaberin B (1) was clearly determined to be a linear dimeric hydroxamate class siderophore. Although compound 1 is an open form of the known macrocyclic dimer Bisucaberin (2), and was previously described as a bacterial degradation product of desferrioxamine B (4), the present report is the first description of the de novo biosynthesis of 1. To the best of our knowledge, compound 1 is the first chemically characterized siderophore isolated from a bacterium belonging to the phylum Bacteroidetes.
Bisucaberin, a new siderophore, sensitizing tumor cells to macrophage-mediated cytolysis. I. Taxonomy of the producing organism, isolation and biological properties
J Antibiot (Tokyo) 1987 Dec;40(12):1664-70.PMID:2962972DOI:10.7164/antibiotics.40.1664.
Alteromonas haloplanktis strain SB-1123 isolated from deep-sea mud produced a new siderophore, Bisucaberin. Bisucaberin rendered tumor cells susceptible to cytolysis mediated by murine peritoneal macrophages which were elicited by Proteose peptone and not yet activated by lymphokine. Bisucaberin exerted its sensitizing activity by both the preincubation with tumor cells and the addition to co-culture of macrophages and tumor cells. The activity of Bisucaberin was specifically inhibited by ferric ion. Bisucaberin showed direct cytostasis for tumor cells but did not cause cytolysis in the absence of macrophages. Cytostasis by Bisucaberin was attributable to the specific inhibition of DNA synthesis in tumor cells.
Bisucaberin biosynthesis: an adenylating domain of the BibC multi-enzyme catalyzes cyclodimerization of N-hydroxy-N-succinylcadaverine
Chem Commun (Camb) 2008 Nov 7;(41):5119-21.PMID:18956041DOI:10.1039/b813029a.
The Bisucaberin biosynthetic gene cluster has been identified in Vibrio salmonicida and a domain from within the BibC multienzyme encoded by the cluster has been shown to catalyse ATP-dependent dimerisation and macrocyclisation of N-hydroxy-N-succinylcadaverine to form Bisucaberin.
Bisucaberin, a new siderophore, sensitizing tumor cells to macrophage-mediated cytolysis. II. Physico-chemical properties and structure determination
J Antibiot (Tokyo) 1987 Dec;40(12):1671-6.PMID:2962973DOI:10.7164/antibiotics.40.1671.
The structure of Bisucaberin, a new siderophore, was determined to be 1,12-dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetron e by spectroscopic analysis and X-ray crystallographic analysis. The molecule of Bisucaberin consists of a cyclic dimer of 1-hydroxy-1,6-diazaundecane-2,5-dione moiety and is closely related to nocardamine, the trimer of the same moiety.